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Jamaica

$99+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated September 15, 2025.

Round-trip from

$342
(Cheapflightsfares)

One-way from

$99
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$540

Good round-trip deal

$491 or less

Good one-way deal

$201 or less
From Chicago (CHI) to Jamaica
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One-way flight from Chicago (CHI) to Jamaica
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Highest demand for flights based on searches. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
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Price to beat on a one-way flight from Chicago (CHI) to Jamaica.
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Find flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Sat 11/151:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/14$342
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:00 pmORD - KIN
2 stops17h 09mSpirit Airlines
Sun 10/1912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Deal found 9/15$373
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:15 amORD - MBJ
Nonstop4h 13mAmerican Airlines
Wed 11/123:13 pmMBJ - ORD
Nonstop4h 41mAmerican Airlines
Deal found 9/14$376
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Sat 10/1812:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
Deal found 9/15$377
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:59 pmORD - MBJ
1 stop17h 06mSpirit Airlines
Thu 12/111:12 pmMBJ - ORD
1 stop11h 30mSpirit Airlines
Deal found 9/15$378
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Sun 12/141:12 pmMBJ - ORD
1 stop11h 30mSpirit Airlines
Deal found 9/13$379
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:44 amORD - MBJ
Nonstop4h 01mAmerican Airlines
Fri 10/1710:20 amMBJ - ORD
1 stop11h 04mAmerican Airlines
Deal found 9/14$380
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:20 amMDW - MBJ
1 stop8h 55mFrontier
Thu 11/64:30 pmMBJ - MDW
1 stop27h 09mFrontier
Deal found 9/15$380
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:48 amORD - MBJ
1 stop6h 24mUnited Airlines
Sat 11/152:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 9/15$381
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:43 pmORD - KIN
1 stop15h 26mSpirit Airlines
Wed 11/51:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/13$381
This CheapOair deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:58 pmORD - MBJ
2 stops16h 02mSpirit Airlines
Fri 10/1712:09 pmMBJ - ORD
1 stop6h 29mSpirit Airlines
Deal found 9/14$382
This Mytrip deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:43 pmORD - KIN
1 stop15h 26mSpirit Airlines
Mon 10/2012:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
Deal found 9/14$382

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Chicago

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 11/8

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Sat 11/15

1:28 pm-9:00 pm

1 stop8h 32m

$342

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/11

6:00 pm-11:09 am

2 stops17h 09m

Kingston Norman Manley

Sun 10/19

12:14 pm-11:45 pm

1 stop11h 31m

$373

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 10/16

6:18 pm-11:09 am

2 stops16h 51m

Kingston Norman Manley

Mon 10/20

12:14 pm-11:45 pm

1 stop11h 31m

$373

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/19

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Tue 11/25

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

10:15 am-3:22 pm

Nonstop4h 07m

Montego Bay Sangster Intl

Sat 12/13

2:26 pm-6:13 pm

Nonstop4h 47m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 11/14

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Mon 11/17

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/31

8:44 am-12:45 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Fri 11/7

2:04 pm-5:40 pm

Nonstop4h 36m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/30

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 12/6

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 11/6

7:56 pm-1:54 pm

1 stop16h 58m

Montego Bay Sangster Intl

Mon 11/10

1:12 pm-11:42 pm

1 stop11h 30m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Tue 12/16

2:48 pm-6:13 pm

Nonstop4h 25m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 58 results
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Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated September 15, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Jamaica?

    A quick flight from Chicago to Jamaica can take about 4h 04m. Spirit Airlines provides one of the quickest options available for as low as $376. There are 1724 mi between Chicago and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $105 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $140 and Southwest from $152 one-way.

  • What are the most popular routes from Chicago to Jamaica?

    The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $661 for a flight from Chicago to Jamaica. The cheapest flight overall is $164 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $261.

  • Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

    Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

  • Can I find deals for business class flights from Chicago to Jamaica?

    Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
Midway to Montego Bay flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
Midway to Providenciales flights
St. Louis to Punta Cana flights
St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Bridgetown flights
St. Louis to Oranjestad flights
St. Louis to Georgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
O'Hare Intl to Puerto Plata flights
St. Louis to Nassau flights
Midway to Simpson Bay flights
Midway to George Town flights
St. Louis to Simpson Bay flights
Midway to Santo Domingo flights
O'Hare Intl to Kralendijk flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Road Town flights
O'Hare Intl to Aguadilla flights
Midway to Castries flights
St. Louis to Willemstad flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Freeport flights
O'Hare Intl to Port of Spain flights
Peoria to Luis Munoz Marin Intl flights
St. Louis to Santo Domingo flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Castries flights
St. Louis to Providenciales flights
O'Hare Intl to Basseterre flights

Top 6 airlines flying from Chicago to Jamaica

Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$438FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$819FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$370Average$446FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$430Average$632FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$447Average$658FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$726FlexibilityNo cancel feeOn-time63%

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